This book forever changed how I work

This was easily one of the most influential books I’ve read in the past three years. I absolutely love Cal’s style of writing. He uses stories and science to illustrate points while making sure the reader comes away with actionable next steps. One of my goals in 2016 is to strike a better work/life balance while simultaneously becoming more productive (writing more, launching more products, etc). Cal outlines a detailed strategy for doing just that in his book Deep Work. He provides very detailed strategies for getting more out of your work hours and limiting distraction. I’ll be writing a separate blog post on exactly how I’m going to apply this book, but you can read a very detailed summary in the reading notes below.


“To remain valuable in our economy, therefore, you must master the art of quickly learning complicated things. This task requires deep work. If you don’t cultivate this ability, you’re likely to fall behind as technology advances.”

“To succeed you have to produce the asbolute best stuff your’e capable of producing — a task that requires depth.”

Why should you focus on deep work?

Cal provides three reasons – Deep work is valuable, rare, and meaningful.

1. Deep Work is Valuable

Two core ability for thriving in the New Economy:

  1. The ability to quickly master hard things
  2. The ability to produce at an elite level, in terms of both quality and speed.

To help answer the question of why deliberate practice works for learning a new skill:

This new science of performance argues that you get better at a skill as you develop more myelin around the relevant neurons, allowing the corresponding circuit to fire more effortlessly and effectively. To be great at something is to be well myelinated.

This understanding is important because it provides a neurological foundation for why deliberate practice works. By focusing intensely on a specific skill, you’re forcing the specific relevant circuit to fire, again and again, in isolation (hence, becoming more myelinated).

Attention residue – “When you switch from some Task A to another Task B, your attention doesn’t immediately follow — a residue of your attention remains stuck thinking about the original task.”

2. Deep Work is Rare

There are three main arguments Cal presents for why deep work is rare:

Shallow work is easier. 

Cal introduces the principle of least resistance, which goes like this:

In a business setting, without clear feedback on the impact of various behaviors to the bottom line, we will tend towards behaviors that are easiest in the moment.

Cultures of connectivity exist because A) getting immediate answers makes your life easier (so you expect others to give you immediate answers) and B) “the culture of connectivity…creates an environment where it becomes acceptable to run your day out of your inbox” (which is an ‘easier’ task that satisfies our goal to feel ‘productive’).

Absence of clear goals leads to busyness for self-preservation. 

He also introduces a concept called busyness as a proxy for productivity – “In the absence of clear indicators of what it means to be productive and valuable in their jobs, many knowledge workers turn back toward an industrial indicator of productivity: doing lots of stuff in a visible manner.” (So very true)

A blinding belief that if a behavior relates to the internet, it must be good.

This describes the blinding philosophy that anything to do with the internet represents forward progress and should be adopted as soon as possible.

3. Deep Work is Meaningful

Cal provides three supporting arguments here:

Neurological argument: Deep work is associated with more meaning

In work (and especially knowledge work), to increase the time you spend in a state of depth is to leverage the complex machinery of the human brain ina  way that for several different neurological reasons maximizes the meaning and satisfaction you’ll associate with your working life.

Psychological argument: Deep work leads to flow

…jobs are actually easier to enjoy than free time, because like flow activities they have built-in goals, feedback rules, and challenges, all of which encourage one to become involved in one’s work, to concentrate and lose oneself in it.

Philosophical argument: Cal presents arguments of craftsman ship, demonstrating that deep work builds meaning and develops pride in your work. He references a craftsman that makes swords and the meaning he gets out of meticulous work.

The first (observation) might be obvious but requires emphasis: There’s nothing intrinsic about themanual trades when it comes to generating this particular source of meaning. Any pursuit — be it physical or cognitive — that supports high levels of skill can also generate a sense of sacredness.

The second key observation about thsi line of argument is that cultivating craftsmanship is necessarily a deep task…

It follows that to embrace deep work in your own career and to direct it toward cultivating your skill, is an effort that can transform a knowledge work job from a distracted, draining obligation into something satisfying…

The Rules

Cal outlines four rules for working deeply:

  1. Work deeply.
  2. Embrace boredom.
  3. Quit social media.
  4. Drain the shallows.

Rule #1: Work Deeply

There are four different schools of thought covered (some more realistic than others):

Monastic – “This philosophy attempts to maximize deep efforts by eliminating or radically minimizing shallow obligations.” (Think seclusion somewhere)

Bimodal – “This philosophy asks that you divide your time, dedicating some clearly defined stretches to deep pursuits and leaving the rest open to everything else.”

Rhythmic – “This philosophy argues that the easiest way to consistently start deep work sessions is to transform them into a simple regular habit.”

Journalistic – “in which you fit deep work wherever you can into your schedule.”

Strategy #1 – Ritualize

Whatever school of thought you choose, each one should have some components:

  • Where you’ll work and for how long.
  • How you’ll work once you start to work – Perhaps a ban on the internet?
  • How you’ll support your work – Maybe you need a good cup of coffee to start or light exercise?

Strategy #2 – Make grand gestures 

Cal recounts the story of J.K. Rowling. As she was trying to write the last book in her Harry Potter series, she found herself distracted and unable to work. So, she spent a good chunk of money on a room in one of the nicest hotels in the city. The act of expending large resources to get setup forces you to want to “make it worth it.” Cal provides an example of how he spent $50 on a mathematical notebook hoping the large price tag would encourage him to work in it.

Strategy #3 – Don’t work alone

This seems counterintuitive to the whole idea of the book, but Cal clarifies specific instances that this could work:

the whiteboard effect…working with someone else at the proverbial shared whiteboard can push you deeper than if you were working alone.

Strategy #4 – Execute like a business

This is further broken down into four sub-strategies:

A. Focus on the wildly important – “If you want to win the ware for attention, don’t try to say ‘no’ to the trivial distractions you find on the information smorgasboard; try to say ‘yes’ to the subject that arouses a terrifying longing, and let the terrifying longing crowd out everything else.”

B. Act on the lead measures – This was a hidden gem that I found incredibly valuable. Most people focus on lag measures, which are directed at a specific outcome. The downside is that once you get to the end, it’s already too late if you are going to fall short. Lead measures “measure the new behaviors that will drive success on the lag measures.”

C. Keep a compelling scoreboard – Cal kept a tally of how many hours he was working deep on any given week.

D. Create a cadence of accountability – Use processes like weekly reviews to celebrate good weeks and understand what led to bad ones.

Strategy #4 – Be lazy

This, again, was broken down even further:

A. Downtime aids insights

…(led the experiments to) introduce unconscious thought theory (UTT)…for decisions that require the application of strict rules, the conscious mind must be involved…for decisions that involve large amounts of information and multiple vague…constraints, your unconscious mind is well suited to tackle the issue.

B. Downtime helps recharge the energy needed to work deeply

C. The work that evening downtime replaces is usually not that important

To help with all of this, Cal suggests using a shutdown ritual every night, which I’ve found super helpful. The ritual helps to circumvent something called “the Zeigarnik effect.”

…describes the ability of incomplete tasks to dominate your attention

Rule #2: Embrace boredom

Whereas the first rule taught us how to integrate deep work into our lives, this rule helps to improve our ability to concentrate.

The most helpful takeaway I gained her was “Don’t take breaks from distraction. Instead take breaks from focus.

Rule #3: Quit social media

Cal isn’t suggesting we all dump social media (although he doesn’t use it). Instead, he’s arguing for a more thoughtful approach to selecting which tools we use. Currently, he argues most are using the any-benefit approach to network tool selection:

You’re justified in using a network tool if you can identify any possible benefit to its use, or anything you might possibly miss out on if you don’t use it.

His argument is we should move towards the craftsman approach to tool selection:

Identify the core factors that determine success and happiness in your personal and professional life. Adopt a tool only if its positive impacts on these factors substantially outweigh its negative impacts.

One exercise he recommends in this section is to identify the main goals in your personal and professional life. Then, list the two or three most important activities that help you satisfy those goals. It’s likely that Twitter will not be in the list of the most important activities (it will likely detract from your ability to complete those activities).

Rule #4: Drain the Shallows

Cal discusses several different strategies here:

A. Schedule every minute of your day. We drastically tend to underestimate our time spent on negative activities (watching TV) and overestimate on positive ones (working).

B. Quantify the depth of every activity. To help quantify the depth of an activity, Cal asks the following question:

How long would it take (in months) to train a smart recent college graduate with no specialized training in my field to complete this task?

C. Ask your boss for a shallow work budget (What percentage of my time should be spent on shallow work?)

D. Finish your work by five thirty. Impose a time constraint.

E. Become hard to reach. The best tactic I pulled from this section is to do more work when you send email. Rather than sending something like “Thoughts?” at the end of an email, take a process-centric approach and make sure to include next steps, who is responsible for those next steps, and a next step deadline.